Butyl isocyanate → HCID 178449558, compound

HRID 1930735Notes

Reaction equation

HRID 1930735 reaction equation
[O:1]([CH2:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][C:19]3[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=3)=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([N:32]=[C:33]=[O:34])[CH2:29][CH2:30][CH3:31].C(#N)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>O1CCCC1>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[CH2:28]([NH:32][C:33]([NH:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:17]2[CH:26]=[CH:27][C:14]([C:12]3[N:13]=[C:9]([CH2:8][O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[NH:10][CH:11]=3)=[CH:15][CH:16]=2)=[CH:25][CH:24]=1)=[O:34])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 21924481TFA acetonitrileHCID 178507748HCID 178507748, compound

Product 1

HCID 178449558HCID 178449558, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing 4-{4-[2-(phenoxymethyl)-1H-imidazol-4-yl]phenoxy}aniline (0.2 g, 0.56 mmol) and butylisocyanate (0.094 g, 0.84 mmol) in 3 ml of tetrahydrofuran is stirred for a day at ambient temperature. Aminomethylpolystyrene resin EHL (Novabiochem, 200-400 mesh, 2% DVB) (200 mg, approximately 1 mmol) is added and stirring is maintained for three hours. After filtration on frit then concentration of the filtrate in a rotavapor, the residue obtained is passed through an RP18 silica column (eluent: acetonitrile-trifluoroacetic acid 0.1N: 5-5); a beige-coloured powder is obtained with a yield of 43%.

Workup

  1. additionAminomethylpolystyrene resin EHL (Novabiochem, 200-400 mesh, 2% DVB) (200 mg, approximately 1 mmol) is added
  2. stirringstirring
  3. temperatureis maintained for three hours
  4. filtrationAfter filtration on frit
  5. customconcentration of the filtrate in a rotavapor, the residue obtained
  6. customa beige-coloured powder is obtained with a yield of 43%

Sources & evidence

ORD record
ord-7c6550e79f5f410ca66305f9bb2f01ad
Source dataset
uspto-grants-2012_05
Patent number
US08188133B2

Reaction notes

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